HCID 398147, compound → 6-(Cyclohexylmethoxy)-5-nitrosopyrimidine-2,4-diamine

HRID 1838958Notes

Reaction equation

HRID 1838958 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([NH2:16])[N:3]=1.[N:17]([O-])=[O:18].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([N:17]=[O:18])=[C:4]([NH2:16])[N:3]=1

Participants

4

Reactant 2

HCID 398147HCID 398147, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 3981486-(Cyclohexylmethoxy)-5-nitrosopyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

2,6-Diamino-4-cyclohexylmethoxypyrimidine (0.28 g, 1.26 mmol) was dissolved in warm glacial acetic acid solution (30%, 10 ml). The solution was heated to 80° C. and sodium nitrite solution (0.12 g, 1.72 mmol in 5 ml of H2O) was added dropwise over 1 h, until and excess of oxidant, as indicated by starch iodide paper, was observed. The reaction mixture was allowed to cool to room temperature and the violet crystals were collected by filtration, and washed well with water. The title compound was purified by recrystallisation from ethanol (0.26 g, 83%), m.p. 254° C.; (Found: C, 52.73; H, 6.59; N, 27.56% C11H17N5O2 requires C, 52.59; H, 6.77; N, 27.89%); δH (200 MHz, d6-DMSO) 1.09-1.38 (5H, m, C6H11), 1.73-2.00 (6H, 5 m, C6H11), 4.39 (2H, d, OCH2, J=6.3 Hz), 7.86 (2H, br s, NH2), 8.08 (1H, br s, NH), 10.19 (1H, br s, NH); m/z (+EI) 251 (M+, 25%), 155 (M+-C7H13 , 100) , 138 (M+-C7H13O, 72) , 81 (9).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe violet crystals were collected by filtration
  3. washwashed well with water
  4. customThe title compound was purified by recrystallisation from ethanol (0.26 g, 83%), m.p. 254° C.

Sources & evidence

ORD record
ord-ec59a1e93eaf45ba97994e468f2bf365
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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